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Fluoride Migration Catalysis Enables Simple, Stereoselective, and Iterative Glycosylation
journal contribution
posted on 2020-04-01, 19:14 authored by Girish
C. Sati, Joshua L. Martin, Yishu Xu, Tanmay Malakar, Paul M. Zimmerman, John MontgomeryChallenges
in the assembly of glycosidic bonds in oligosaccharides
and glycoconjugates pose a bottleneck in enabling the remarkable promise
of advances in the glycosciences. Here, we report a strategy that
applies unique features of highly electrophilic boron catalysts, such
as tris(pentafluorophenyl)borane, in addressing a number of the current
limitations of methods in glycoside synthesis. This approach utilizes
glycosyl fluoride donors and silyl ether acceptors while tolerating
the Lewis basic environment found in carbohydrates. The method can
be carried out at room temperature using air- and moisture-stable
forms of the catalyst, with loadings as low as 0.5 mol %. These characteristics
enable a wide array of glycosylation patterns to be accessed, including
all C1–C2 stereochemical relationships in the glucose, mannose,
and rhamnose series. This method allows one-pot, iterative glycosylations
to generate oligosaccharides directly from monosaccharide building
blocks. These advances enable the rapid and experimentally straightforward
preparation of complex oligosaccharide units from simple building
blocks.
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monosaccharide building blocksoligosaccharide unitsmethodmoisture-stable formselectrophilic boron catalystsadvanceiterative glycosylationsbuilding blocksglycosylation patternssilyl ether acceptorsglycosyl fluoride donorsIterative Glycosylation Challengesglycoside synthesisrhamnose seriesFluoride Migration Catalysis Enablesroom temperatureglycosidic bonds
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